One-Week Italy Self-Drive Road Trip With Itinerary from Florence traveling south to Siena and Pienza

Day 2 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Piazzale Michelangelo is the perfect place to start. This observation deck is one of the most spectacular places to visit in Florence. Next, head to Basilica Of Santa Croce In Florence, a captivating church, known for its standout features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Uffizi Gallery. This picture-perfect art gallery is a highly recommended experience. Nearby, you'll also find Ponte Vecchio and Piazza Della Signoria. Visit these for an interesting touch to your journey. Finish the day with a visit to Galleria Dell'accademia, a photogenic art gallery in Florence.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Experience shopping bliss at Florence as you explore San Lorenzo Market. Take a leisurely stroll through unique and shops, where local treasures are waiting to be found. Beyond shopping, San Lorenzo Market offers more options, including unique attractions, key services, and vibrant events.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 3 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in San Gimignano. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Porta San Giovanni. This culturally significant monument is sure to ignite your curiosity. Next, dive into the inviting features of Piazza Del Duomo, a must-visit public square in the village.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Palazzo Comunale, Pinacoteca, Torre Grossa, a frequently visited museum. For a change of scene, check out Rocca Di Montestaffoli, known for its visually striking features. We also recommend visiting Parco Della Rocca. This park is a must for anyone looking to experience the village to the fullest.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat in Siena. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena is also a great option that provides a perfect setting for a relaxing evening.

Say good night to Siena and look forward to another great day of your road trip in Italy!

On day 4 of your road trip, you will have an entire day to explore Siena. You’ll stay in Siena for 1 night and discover all the best things to see and do in the area.

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Pubblico Palace. This picture-perfect palace is a highlight of any visit in the city. Then, enjoy Tower Of Mangia, another picture-perfect attraction that never fails to captivate visitors. Next, head over to Piazza Del Campo, one of the city’s most impressive attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Siena Cathedral. This visually striking church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Basilica Of San Domenico, a curiosity-inducing church, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Fortezza Medicea (siena) before you head back to your hotel.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Make sure to reserve a table at Osteria Quattro Venti, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Fischi per Fiaschi, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your meal, keep the night alive at a bar like Charlie Mixology Bar Di Aldinucci Riccardo, known for its lively atmosphere. Bar Pinacoteca is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, San Paolo Pub offers an excellent atmosphere for those looking to amp up the evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Pienza and San Quirico d'Orcia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pienza. You will spend 2 nights here for some well-deserved relaxation.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the up-and-coming Palazzo Piccolomini, Pienza, a visually striking palace in Siena. Next, go to Cipressi Di San Quirico D'orcia.

After visiting Palazzo Piccolomini, Pienza and Cipressi Di San Quirico D'orcia, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Chapel Vitaleta. This respected church offers a unique experience.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Pienza. Pienza offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Pienza. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Raise your glass to another unforgettable day in Italy!

Wake up to day 6 of your extraordinary road trip in Italy. With 1 night left in Pienza, we encourage you to seize the day and discover the unexplored beauty of the village’s surroundings!

Bring your curiosity for today’s adventure around Pienza. Some of the town’s most loved attractions await! Porta Al Prato is the perfect place to start. This monument is one of the most intriguing places to visit in Pienza. Next, head to Fortezza Medicea, an underrated castle, known for its romantic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Fortress Of Montalcino. This history-steeped castle is a highly recommended experience. Nearby, you'll also find Abbey Of Sant'antimo. Visit these for an interesting touch to your journey.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Pienza.

Indulge in a memorable dining experience at one of Pienza's most popular restaurants, and connect with friendly locals for an authentic adventure.

Take some time to reflect on your day and savor another beautiful night in Italy.

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Arezzo, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Pienza, featuring family-friendly attractions, photo-friendly spots, and historic treasures. Start at San Francesco, Arezzo, an underrated church in the city. Then, head to Fondazione Ivan Bruschi - Casa Museo Dell'antiquariato Ivan Bruschi and soak in the ambiance of this photogenic museum.

There are many interesting places to see in Pienza, and when you are ready for more, go to Piazza Grande. This is one of the city’s most locally renowned visually striking spots of interest. After exploring the public square, visit the increasingly popular Arezzo Cathedral.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Make sure to reserve a table at Ristorante Buca Mario, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Agricola Toscana, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Gosh* after your meal, a hub for lively evenings and memorable moments. Or, head to Antico Caffè Del Moro - Art Bar Firenze for a great selection of flavorful drinks and a charming setting. Furthermore, Quelo Bar is perfect for those looking to extend their night with a touch of local flavor.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!